ORGLIST: Condensation with Nitromethane-2

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From: kmorendha (mailbox$##$prolificint.com)
Date: Thu Jun 08 2006 - 09:51:41 EDT


Hi friends !

In continuation to my earlier posting, I again tried this Condensation step converting my arylaldehyde to its nitroethanol derivative with some other route.

Recently I came across one US patent in which aldehyde was being converted to its bisulphite adduct using sodium bisulphite & then it was condensed with separately prepared sodium salt of nitromethane (prepared from dissolving nitromethane in eq. molar NaOH aq. solution).

But when I tried this procedure, after the condensation, I got my aldehyde back from that reaction mixture !! Here, I think after addition of Na-Nitromethane solution, the adduct breaks down again to the aldehyde due to alkalinity.... Is it so ?

Here, I must say, this process is a nice route for me (if it works !) because as my reactant arylaldehyde is having OH group & it can be only converted to its nitroethanol derivative by first protecting this OH group by acetylating it & then condensing. But by this process, I may directly convert the OH-aldehyde to its OH-nitroethanol derivative.

Pls try to understand my problem carefully & let me suggest some solution for doing this task !!

Regards,
Kamal


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